TREA

Degradation and detoxification of halogenated olefinic hydrocarbons

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Information

  • Patent Grant
  • 4468297
  • Patent Number
    4,468,297
  • Date Filed
    Friday, February 25, 1983
    41 years ago
  • Date Issued
    Tuesday, August 28, 1984
    40 years ago
Information
Abstract
Description
Claims
  • providing an electrolytic cell fitted with an anode and a cathode and containing an aprotic solvent selected from the group consisting of dimethylformamide or acetonitrile adjacent the cathode, the aprotic solvent containing an electrolyte soluble therein and being substantially free of water;
  • adding the hydrocarbon compound to said aprotic solvent;
  • electrolytically generating superoxide ion at the cathode to react with the hydrocarbon compound to form a degradation product thereof, the degradation product reacting with the aprotic solvent to form chloride ion and bicarbonate; and
  • removing said chloride ion and bicarbonate from the electrolytic cell.
US Referenced Citations (1)
Number Name Date Kind
3677916 Seiber et al. Jul 1972
Non-Patent Literature Citations (24)
Entry
"The Chemistry of Superoxide Ion", Sawyer, D. T. & Gibian, M. J.; Tetrahedron, vol. 35, 1979, pp. 1471-1481.
"Electrochemical Studies of the Reactivity of Superoxide Ion With Several Alkyl Halides in Dimethyl Sulfoxide", Merritt, M. V., Sawyer, D. T.; Journ. of Organic Chemistry, 35, 1970, pp. 2157-2159.
"Nucleophilic Reactions of Electrogenerated Superoxide Ion", Dietz, R.; Forno, A. E. J.; Larcombe, B. E. & Peover, M. E.; Journ. Chem. Soc., B, 1970, pp. 816-820.
Dietz et al., Chemical Abstracts vol. 72, Abstract 85626t (1970).
Fleischmann et al., Chemical Abstracts, vol. 70, Abstract 56925t (1969).
"The Reaction of Superoxide with Alkyl Halides and Tosylates", Chern, C-I.; San Filippo, Jr., J.; Valentine, J. S.; J. Org. Chem., vol. 40, No. 11, 1975, pp. 1678-1680.
"Superoxide Chemistry. A Convenient Synthesis of Dialkyl Peroxides"; Johnson, R. A.; Nidy, E. G.; J. Org. Chem., vol. 40, No. 11, 1975, pp. 1680-1681.
"Cleavage of Esters by Superoxide"; Chern, C-I.; San Filippo, Jr., J.; Romano, L. J.; J. Org. Chem., vol. 41, No. 3, 1976, pp. 586-588.
"On the Reaction Kinetics of Electrogenerated Superoxide Ion with Aryl Benzoates"; Bontempelli, G.; Magno, F.; J. Electroanal. Chem., 68, 1976, pp. 337-344.
"Reactivity of Superoxide Ion with Carbonyl Compounds in Aprotic Solvents"; Gibian, M. J.; Morrison, M. M.; Sawyer, D. T.; Tangpoonpholvivat, R.; Ungermann, T.; J. American Chem. Soc., 101:3, 1979, pp. 640-644.
"A Study of the Reaction Kinetics of Electrogenerated Superoxide Ion with Benzylbromide"; Magno, F.; Seeber, R.; Valcher, S.; J. Electroanal. Chem., 83, 1977, pp. 131-138.
"Nucleophilic Reactions of Superoxide Anion Radical"; Arudi, R. L.; Danen, W. C.; Warner, R. J.; Organic Free Radicals, ACS Symposium Series 69; Prior, W. A., ed.; 1978, pp. 244-257.
"The Electrochemical Reduction of Superoxide Ion and Oxidation of Hydroxide Ion in Dimethyl Sulfoxide"; Goolsby, A. D.; Sawyer, D. T.; Analytical Chemistry, vol. 40, No. 1, 1968, pp. 83-86.
Advanced Organic Chemistry; March, J.; 2nd ed.; McGraw-Hill, N.Y., 1977, pp. 342-343.
"Mechanisms of protection against the damage produced in biological systems by oxygen-derived radicals"; Slater, T. F.; Oxygen Free Radicals and Tissue Damage; Ciba Foundation Symposium 65; Elsevier/North-Holland: N.Y., 1979, pp. 143-163.
Experimental Electrochemistry for Chemists; Sawyer, D. T.; Robert, J. L., Jr.; John Wiley & Sons, New York, 1974, pp. 167-215 (Chapter Four).
"Chemical and Physical Properties of Superoxide", Fee, J. A. and Valentine, J. S.; Superoxide and Superoxide Dismutases, Academic Press, 1977, pp. 19, 53, 58.
Allen, Organic Electrode Processes, pp. 90, 91, pub. by Chapman & Hall Ltd., London (1958).
Rifi et al., Introduction to Org. Electrochem, pp. 214, 215, pub. by Marcel Dekker, Inc., N.Y. (1974).
Fry et al., "Electrolyte Effects upon the Polarographic Reduction of Alkyl Halides in Dimethyl Sulfoxide", J. Org. Chem., vol. 41, No. 1, pp. 54-57 (1976).
"How Super is Superoxide?", Sawyer, D. T. et al., Acc. Chem. Res. 14, pp. 393-400 (1981).
LeBerre, A.; Berguer, Y., Bull. Soc. Chem. Fr., pp. 2363-2374 (1966).
Schmidt, M.; Bipp, H., Z. Anorg. Ally. Chem., 303, pp. 190-200 (1960).
"The Reaction of Superoxide Anion Radical With Electron Poor Olefins", Frimer et al., Tetrahedron Lett